Glyoxal

Formula: C₂H₂O₂
Molecular weight: 58.0361
IUPAC Standard InChI: InChI=1S/C2H2O2/c3-1-2-4/h1-2H
IUPAC Standard InChIKey: LEQAOMBKQFMDFZ-UHFFFAOYSA-N
CAS Registry Number: 107-22-2
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: Ethanedial; Biformal; Biformyl; Diformyl; Ethanedione; Glyoxal aldehyde; Glyoxylaldehyde; Oxal; Oxalaldehyde; 1,2-Ethanedione; (CHO)2; Diformal; Ethane-1,2-dione; Ethandial; Aerotex glyoxal 40; ODIX; Protectol GL 40
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Information on this page:
Other data available:
Data at other public NIST sites:
- Computational Chemistry Comparison and Benchmark Database
- Gas Phase Kinetics Database
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Gas phase thermochemistry data

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Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity	Value	Units	Method	Reference	Comment
Δ_fH°_gas	-212.0 ± 0.79	kJ/mol	Cm	Fletcher and Pilcher, 1970	ALS
Quantity	Value	Units	Method	Reference	Comment
Δ_cH°_gas	-860.90 ± 0.75	kJ/mol	Cm	Fletcher and Pilcher, 1970	Corresponding Δ_fHº_gas = -212.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS

Constant pressure heat capacity of gas

C_p,gas (J/mol*K)	Temperature (K)	Reference	Comment
36.36	50.	Thermodynamics Research Center, 1997	p=1 bar. Recommended entropies and heat capacities are in close agreement with other statistically calculated values [ Compton D.A.C., 1977, Hollenstein H., 1980]. Calculation [ Natarajan A., 1982] seems to be erroneous.; GT
41.42	100.
45.95	150.
50.49	200.
57.63	273.15
60.23	298.15
60.43	300.
71.21	400.
81.43	500.
90.12	600.
97.05	700.
102.44	800.
106.61	900.
109.86	1000.
112.44	1100.
114.52	1200.
116.22	1300.
117.63	1400.
118.8	1500.

Phase change data

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Data compiled by: Robert L. Brown and Stephen E. Stein

Quantity	Value	Units	Method	Reference	Comment
T_boil	323.6	K	N/A	Weast and Grasselli, 1989

Gas phase ion energetics data

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Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
B - John E. Bartmess

View reactions leading to C₂H₂O₂⁺ (ion structure unspecified)

Quantity	Value	Units	Method	Reference	Comment
IE (evaluated)	10.2	eV	N/A	N/A	L

Electron affinity determinations

EA (eV)	Method	Reference	Comment
0.62 ± 0.26	R-A	Compton, Reinhardt, et al., 1983	From ethylene carbonate; G3MP2B3 calculations indicate an EA of ca. 1.0 eV; B

Ionization energy determinations

IE (eV)	Method	Reference	Comment
10.2	PE	Buhl, Kramme, et al., 1991	LL
10.21	PI	Traeger, 1985	LBLHLM
9.48 ± 0.08	EI	Reed and Brand, 1958	RDSH
10.60 ± 0.05	PE	Verheijdt and Cerfontain, 1982	Vertical value; LBLHLM
10.60	PE	Kimura, Katsumata, et al., 1981	Vertical value; LLK
10.6	PE	Von Niessen, Bieri, et al., 1980	Vertical value; LLK
10.52	PE	Arnett, Newkome, et al., 1974	Vertical value; LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
CHO⁺	11.20	HCO	PI	Traeger, 1985	LBLHLM
CHO⁺	12.72 ± 0.12	CHO	EI	Reed and Brand, 1958	RDSH

References

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Fletcher and Pilcher, 1970
Fletcher, R.A.; Pilcher, G., Measurements of heats of combustion by flame calorimetry, Trans. Faraday Soc., 1970, 66, 794-799. [all data]

Thermodynamics Research Center, 1997
Thermodynamics Research Center, Selected Values of Properties of Chemical Compounds., Thermodynamics Research Center, Texas A&M University, College Station, Texas, 1997. [all data]

Compton D.A.C., 1977
Compton D.A.C., Values for the gas-phase thermodynamic functions of conjugated compounds existing as a mixture of conformers, J. Chem. Soc. Perkin Trans. 2, 1977, 1307-1311. [all data]

Hollenstein H., 1980
Hollenstein H., Sum of states, isomeric group and symmetry number of nonrigid molecules, Chem. Phys., 1980, 47, 269-285. [all data]

Natarajan A., 1982
Natarajan A., Vibrational analysis of glyoxal-h2, -d2 and -hd, J. Indian Chem. Soc., 1982, 59, 1156-1157. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Compton, Reinhardt, et al., 1983
Compton, R.N.; Reinhardt, P.W.; Schweinler, H.C., Formation of gas-phase negative ions in vinylene carbonate, Int. J. Mass Spectrom. Ion Phys., 1983, 49, 113. [all data]

Buhl, Kramme, et al., 1991
Buhl, M.; Kramme, R.; Martin, H.; Mayer, B.; Nowack, G., Konformation und lichtabsorption von hexa-1,5-den-3,4-dion (divinylglyoxal), Chem. Ber., 1991, 124, 821. [all data]

Traeger, 1985
Traeger, J.C., Heat of formation for the formyl cation by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1985, 66, 271. [all data]

Reed and Brand, 1958
Reed, R.I.; Brand, J.C.D., Electron impact studies. Part 4. Glyoxal, methylglyoxal and diacetyl, J. Chem. Soc. Faraday Trans., 1958, 54, 478. [all data]

Verheijdt and Cerfontain, 1982
Verheijdt, P.L.; Cerfontain, H., Dipole moments, spectroscopy, and ground and excited state conformations of cycloalkane-1,2-diones, J. Chem. Soc. Perkin Trans. 2, 1982, 1541. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Von Niessen, Bieri, et al., 1980
Von Niessen, W.; Bieri, G.; Asbrink, L., 30.4 nm He(II) photoelectron spectra of organic molecules. Part III. Oxo-compounds (C,H,O), J. Electron Spectrosc. Relat. Phenom., 1980, 21, 175. [all data]

Arnett, Newkome, et al., 1974
Arnett, J.F.; Newkome, G.; Mattice, W.L.; McGlynn, S.P., Excited electronic states of the α-dicarbonyls, J. Am. Chem. Soc., 1974, 96, 4385. [all data]

Notes

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Symbols used in this document:

AE	Appearance energy
C_p,gas	Constant pressure heat capacity of gas
EA	Electron affinity
IE (evaluated)	Recommended ionization energy
T_boil	Boiling point
Δ_cH°_gas	Enthalpy of combustion of gas at standard conditions
Δ_fH°_gas	Enthalpy of formation of gas at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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